Naked Houseboy & his BBW Boss Ch. 18

Part 18 of an ongoing story...

The previous day was our first experience with the new chastity device. But I had only worn it for a few minutes. This day would be the first real test. Carrie and I agreed that I would only wear it while she was at work. That was more than enough for the first day.

When Carrie came downstairs to the kitchen before work, I was waiting for her as usual. In my left hand, I held her cup of coffee. In my right, the chastity device. As she took the coffee from me, she eyed the metal cage.

"Are you sure you want to do this?" she asked softly.

"Want is a strong word," I admitted. "But it's for the party, right?" In two weeks, we would be hosting her best friends for a dinner party as a way to introduce them to her naked houseboy. I had decided it would be best for me to be caged up at said party, so as to avoid any...distractions.

"I suppose so," she shrugged. "Well, go on."

At her instruction, I fitted the ring behind my balls and attached the cage over my penis. With a deep breath, I turned the key. I was locked in.

"You OK?" she asked.

"I'm fine," I nodded, handing her the metal chain with the key. She took it and hung it around her neck. Then she took the key and tucked it into her shirt. The chain was hardly visible. Now the key to the cage around my cock was resting between her massive breasts. I tried not to think about it.

"Alright, I'd better get to work," she said, finishing her coffee. "But listen, if there's any problems, if you're in any pain, call me, OK? I'll come straight home."

"Thanks, Car, but I'm sure that won't be necessary." I wasn't actually sure, but I didn't want her to worry.

"Don't be a hero," she winked. "I'll see you this evening." With that, she turned to go. But when she got to the doorway, she turned around. She just looked at me. More to the point, she was looking at my cage-enclosed dick. She bit her lip and made a face that didn't hide how she felt. I knew she didn't love seeing me like this. And honestly, I didn't love it either. But I was committed. We were committed. Without another word, she turned and left.

The day itself was...interesting. I had been living there for over six months now, and this was the very first day that I didn't masturbate while Carrie was at work. That was strange enough. On top of that, I knew that I wouldn't be able to fall asleep for my usual nap without jerking off first. So I just got straight to work.

Strangely, or maybe not so strangely after all, it was probably the most productive day I'd yet had there. Obviously I was frustrated by my inability to wank, but I turned that frustration to cleaning. In the end, it actually wasn't that bad. Don't get me wrong, it wasn't fun or anything. But I kept myself sufficiently busy that the day went by really rather quickly. In fact, I was still working when Carrie pulled into the driveway. I didn't even know she was home until I heard the door open.

"Jack?" she called. She was probably surprised that I wasn't waiting in the kitchen for her with her glass of wine.

"Be right there!" I called back. As I walked into the kitchen, she was already pulling a wine glass out of the cabinet. She paused just before closing the cabinet door, peering inside. She turned to me. "Jack? Did you...clean in the inside of the cabinets?"

"Uh-huh," I nodded.

"I'm impressed," she smiled, closing the cabinet and pouring herself a glass. "So, how was your day? Are you OK?"

"I'm fine, thanks," I shrugged. "My day wasn't bad really. Actually, I got quite a lot done."

"I can see that! Tell me more!"

"I mean, there's not much to tell. I just figured, the only way to get through a day without masturbating was to keep busy. So that's what I did. I dusted things I didn't even know we had. Also, you know how the sink in your bathroom drips? I took care of that," I added proudly.

"You're an angel! Come here," she opened her arms wide.

"Umm, maybe you could let me out first?" I suggested.

"Oh my god, of course! I'm sorry, Jack. What was I thinking?" Pulling the key out of her blouse she began to approach me. Then she stopped.

"Actually, do you mind if I have a look first?" she asked, nodding towards my crotch.

"Not at all."

She came closer and crouched down into her usual 'inspection' position and proceeded with her usual poking and prodding.

"Does any of this hurt?"

"No, it's fine actually."

"Hmm. Your balls are maybe a little more swollen than usual, but otherwise everything looks normal." These comments were more for herself than for me. Then she stood up and handed me the key. I wasted no time unlocking the cage and freeing myself from the device. "Now?" she asked.

Without answering, I wrapped my arms around her and she embraced me in a big bear hug, pressing her massive bosom against me. This time I didn't even try to hide my instant hard-on.

"Well that didn't take long," she giggled in my ear.

"What did you expect?" I asked.

"This, actually." And she giggled again. But she didn't let go, not the least bit troubled feeling my erection pressed against her. "I'm glad today wasn't too hard...I mean, difficult...for you." More giggling. "Seriously though, I'm really impressed. And I mean it when I say I'm glad today was OK. I was worried about you." With that, she released me from the hug and went to pour herself a second glass of wine.

"Come on," she added. "Let's go into the living room so you can take care of yourself." Moments later, we were seated in our usual spots; she on the sofa, me on the easy chair. I was already holding my dick.

"Listen," I said. "I want to ask you about your day. But maybe first I can just..."

"Don't let me stop you," she grinned.

"Thanks." I closed my eyes and pictured...well, nothing. I just enjoyed the feeling of being able to touch myself again. It didn't take long. I was gone in sixty seconds, as it were, blasting a massive load all over my chest and belly. With a deep, satisfied sigh, I leaned back in the chair, taking a moment to come back to myself. When I opened my eyes again, I found Carrie looking at me with a different kind of satisfied smile.

"You know what I like?" she asked.

"What's that?"

"I like how you're never in a rush to clean yourself off after you finish," she said matter of factly.

"You do? Why's that?"

"Well, and don't let this go to your head, but you look nice with cum all over your chest. But more to the point," she hurried on, allowing the compliment no air, "I take it as a sign of how comfortable you are with yourself. I mean, I have the impression that a lot of people feel shame or are embarrassed after they masturbate. Like they're always in a rush to close their browser window or wipe themselves off, you know? But you're not like that. You're just like, 'this is who I am and I'm totally comfortable with that.' And I just think that's really cool." She smiled warmly.

"Well, thanks C!" She was right though. I did like feeling my own cum against my skin. For the reasons she said, sure. Like it was the mark of a job well done. But also, in a way, it was like my wank session wasn't fully over until I cleaned myself off. And why would I want to rush that? I was happy to sit with Carrie, cum dripping down my chest. And now that I knew she liked seeing me this way, you couldn't pay me to reach for the Kleenex.

"Umm, anyway," I started, clearing my throat. "How was your day?"

"Worse than yours, I'm afraid," she frowned.

"Oh no, what happened?"

"Nothing happened," she shook her head. "I was just worried about you, like I said. The whole day, all I could think about was you being locked up in that thing and how you must be feeling. And knowing that I had the key and was far away. Honestly, it was a little stressful." She blushed at the admission. "But now that I know you were fine and actually did better than just 'OK,' I feel a lot better." She smiled.

"Aww, I'm sorry, Car. I mean, I never wanted to cause you any worry." My words were sincere.

"Oh, I know that. But still, you know? Anyway, it's over now."

"At least until tomorrow," I corrected.

"Are we doing this again tomorrow?"

"Well, part of the idea of practicing with this thing was, I thought you needed to get used to being around me with it on. So I was thinking for tomorrow, instead of me wearing it while you're at work, I should put it on when you get home. And you know, just wear it for the evening."

"Oh," she furrowed her brow. "I guess you're right. If that's what you think we should do..."

"I do."

"Alright then." She paused. "Hey, I was thinking about watching a movie tonight. Any interest?"

"Honestly? I'm pretty sure the only thing I want to do this evening is masturbate as much as possible.

"Oh right!" she said with a laugh. "Obviously! Well you've certainly earned it." She started to get up. "So I'll leave you to it then."

"Did I ask you to leave?" I said sharply, reversing the roles from the day before. The tone of my voice caught her off guard for just a moment.

"Well, I just figured you'd want to be alone," she shrugged, standing to her full height.

"Really? Do you think I took a job as naked houseboy just to go and hide every time I want to masturbate?" She looked at me with a wicked grin, loving how I had turned her own game against her. I was loving it too. The banter was turning me on and I started playing with my stiffening dick.

"How the hell should I know?" she spat, sitting back down on the sofa. "Look at you, sitting by yourself in that easy chair. I could be in another room, for all you care. If you wanted me around, I figure you'd show me!"

"What, like come and sit next to you on the sofa?" I raised an eyebrow.

"That'd be a start," she rolled her eyes in mock annoyance.

"If that'll shut you up," I sneered. A moment later, I was sitting beside her on the couch, stroking my cock, maybe two inches between us. But that wasn't enough for Carrie. She pushed herself right up against me, closing the gap. And then she wrapped her arm around my shoulder. I was pumping my dick energetically.

"So you like having me around when you masturbate, is that what you're trying to say?" she whispered in my ear.

"I love having you around when I masturbate," I corrected.

"So? Show me." That was all the encouragement I needed. I closed my eyes and felt my body shudder as I exploded for the second time. Yesterday when we had played this game, she had left the kitchen right after I came. And that's what I was expecting this time. Instead, she stayed close to me, her arm around my far shoulder. And she rested her head against my other shoulder.

"Now you're wearing two loads," she commented, looking down at my chest.

"Does it still look good?" I inquired.

"Two is always better than one," she giggled softly before falling silent.

It had been a long day, I realized. I had had my usual nap, I had worked twice as hard as usual and now, finally, I had jerked off twice. I was exhausted. Carrie must have had a long day too. Tilting my head slightly, I could see that her eyes were closed. The slow and steady rise and fall of her enormous bosom showed that she had indeed fallen asleep.

"Why not?" I thought, closing my own eyes. The sofa was soft and comfortable, Carrie's body, even dressed for work, was soft and warm against my naked flesh. I really didn't want to be anywhere else. Smiling to myself, I let sleep take me...